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Tauroursodeoxycholic acid (TUDCA)

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Identification
Molecular formula
C26H45NO6S
CAS number
14605-22-2
IUPAC name
2-[4-[(3R,5R,8R,9S,10S,12S,13R,14S,17R)-3,12-dihydroxy-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]pentanoylamino]ethanesulfonic acid
State
State
Tauroursodeoxycholic acid is typically a solid at room temperature, appearing as a white crystalline powder.
Melting point (Celsius)
216.00
Melting point (Kelvin)
489.15
Boiling point (Celsius)
0.00
Boiling point (Kelvin)
0.00
General information
Molecular weight
499.69g/mol
Molar mass
499.6850g/mol
Density
1.4000g/cm3
Appearence
Tauroursodeoxycholic acid appears as a white crystalline powder that is soluble in water.
Comment on solubility

Solubility of 2-[4-[(3R,5R,8R,9S,10S,12S,13R,14S,17R)-3,12-dihydroxy-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]pentanoylamino]ethanesulfonic acid

This compound, with its intricate structure, presents interesting characteristics regarding solubility. Its solubility properties can be influenced by several factors:

  • Polarity: The presence of sulfonic acid groups generally indicates a higher degree of polarity, leading to increased solubility in polar solvents, such as water.
  • Hydrogen Bonding: The hydroxyl (-OH) groups also enhance solubility through hydrogen bonding capabilities, allowing interaction with solvents.
  • Chain Length: The long hydrocarbon chain might introduce some hydrophobic character, which can limit solubility in purely aqueous environments but could enhance solubility in organic solvents.
  • pH Dependence: As a sulfonic acid, the solubility can be influenced by the pH of the solution; at lower pH levels, it is more likely to remain protonated and soluble.

To summarize:

  • The compound is likely soluble in water due to its polar characteristics.
  • It may exhibit variable solubility in different organic solvents.
  • The pH of the solution can significantly affect its overall solubility.

In conclusion, this complex molecule displays favorable solubility properties in polar solvents while exhibiting some limitations in more hydrophobic environments, making it multidimensionally soluble.

Interesting facts

Interesting Facts about 2-[4-[(3R,5R,8R,9S,10S,12S,13R,14S,17R)-3,12-dihydroxy-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]pentanoylamino]ethanesulfonic acid

This compound is a fascinating example of how complex organic molecules can be synthesized through intricate chemical pathways. Its structure highlights the connectivity and arrangement of various functional groups, making it a notable study subject in organic chemistry and biochemistry.

Key Highlights:

  • Biological Relevance: This compound has potential implications in biological systems, particularly relating to membrane dynamics due to its sulfonic acid group.
  • Applications: Compounds similar to this one could play crucial roles in pharmaceuticals, perhaps as therapeutic agents or in drug delivery mechanisms.
  • Synthesis Challenge: The multi-step synthesis required to create such a molecule presents a remarkable challenge to chemists, emphasizing the creativity and skill involved in organic synthesis.
  • Chirality: The presence of multiple stereogenic centers (indicated by the 'R' and 'S' designations) leads to chirality, making the study of its enantiomers a pivotal aspect of research.
  • Structural Complexity: The tetradecahydrophenanthrene structure suggests significant interest in its conformation and interactions within biological systems.

Moreover, one can appreciate how compounds like this one can act as a bridge between organic chemistry and the life sciences, facilitating a deeper understanding of cellular processes. The combination of the diverse chemical functionalities not only broadens potential applications but also adds layers of intrigue to the study of such a compound.

In the words of renowned chemist Linus Pauling, "The best way to have a good idea is to have lots of ideas." This compound embodies that spirit, showcasing the beautiful intertwining of creativity and scientific inquiry.

Synonyms
Ethanesulfonic acid, 2-(((3alpha,5beta,12alpha)-3,12-dihydroxy-24-oxocholan-24-yl)amino)-
UNII-20668G0RPI
SCHEMBL15049189
PD162598
DB-227011
NS00120261